16 East Trail

Darien, CT
$ 7,950,000 Beds 9 Baths 8.5 Sq 8,188
Monthly Estimate* How much can I afford?

Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the home's historic integrity while introducing refined, livable spaces. Interiors by acclaimed designer Katie Ridder bring a fresh yet classic sensibility, blending color, texture, and bespoke detail throughout. The main residence offers 7 bedrooms and 6 full baths, anchored by five fireplaces that add warmth and character across its gracious living spaces. A classic carriage house offers a fully equipped 2-bedroom, 1-bath guest residence with its own kitchen, providing exceptional flexibility-ideal for extended stays, in-law living, or a private home office retreat. The grounds, designed by renowned landscape architect Janice Parker, are a true highlight-lush, structured, and beautifully layered for year-round interest. An in-ground saltwater pool completes the estate-like setting, creating a private retreat perfect for both entertaining and quiet enjoyment. Rich in history and elevated by a world-class design team, 16 East Trail offers a rare opportunity to own a piece of Darien's architectural legacy-seamlessly tailored for modern living.

Single Family

  • Price
  • $ 7,950,000
  • City
  • Darien
  • Bedrooms
  • 9
  • Full Bathrooms
  • 7
  • County
  • Fairfield
  • Half Bathrooms
  • 3
  • Area
  • Lot Size
  • 2.89 Acres
  • Zip
  • 06820
  • Sqr Footage
  • 8,188
  • Year Built
  • 1908
  • Taxes
  • $ 61105
  • Style
  • MLS#
  • 24168537
Listed By: Ashley Dineen 203-253-9616 with Compass Connecticut, LLC. - (203) 423-3100
Data Source: Smart MLS

Features

General

Zoning R-1
Neighborhood Tokeneke
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.89
Directions Old Farm Rd to East Trail
High School Darien
City Darien
Elementary School Tokeneke
Sq Ft Total 8188
DOM 134
Year Built 1908
Exclusions See Listing agent for exclusion sheet
Style Colonial
Year Built Source Public Records
Pool Description Gunite,Heated,Salt Water,In Ground Pool
Association Fee Includes Security Service,Snow Removal,Road Maintenance

Interior Features

Cooling System Central Air
Total Rooms 21
Basement Description Full,Partially Finished,Full With Walk-Out

Exterior Features

Water Source Public Water Connected
Lot Description Professionally Landscaped

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Tokeneke Elementary School
Middle School Unknown Middle School
High School Darien High School

Price History

4/20/2026 Listed $8,995,000
5/21/2026 6% - $8,495,000
9/1/2026 6% - $7,950,000

Property vs Zip Code Average in 06820

Price
AVG $4.29M
$7.95M
Year Built
AVG 1948
1908

16 East Trail Darien, CT is a Single Family Home for sale at $7950000 with 8188 sqft and a lot size of 2.89 Acres Acre(s). 16 East Trail Darien has 9 bedrooms, 7 baths and was built in 1908. The property's zip code is 06820 which is in Darien, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.